You really can't get a correct answer on how difficult it is as there will be varying degrees of experience and abilities. Heck I have a buddy who has trouble changing lanes in a small car in traffic. I wouldn't blink twice at taking a 27 footer anywhere, that's tiny to me. I used to drive a 40ft hazmat truck around NYC, lucky for me all those flammable and explosive signs made people a little wary about doing something stupid. :) If you don't have the ability then pick the correct hours to travel and you'll be more then fine.
